Chiral acetals as stereoinductors: Diastereoface selective alkylation of dihydrobenzoxazine-derived amide enolates

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6540-6546

  Mulzer, Johann ^a   Langer, Oliver ^a   Hiersemann, Martin ^b   Bats, Jan W ^c   Buschmann, Jürgen ^d   Luger, Peter ^d  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

^b DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^c GOETHE UNIVERSITY   (Germany)

^d FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; AMIDE; AMINOALCOHOL; BENZOXAZINE DERIVATIVE; CARBON;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0034613229     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000352o     Document Type: Article

References (46)

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15. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195- 2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970- 11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
16. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195- 2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970- 11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
17. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195- 2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970- 11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
18. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195- 2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970- 11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
19. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195- 2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970- 11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
20. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195-2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970- 11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
21. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195- 2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970-11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
22. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195- 2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970- 11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
23. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195- 2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970- 11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
24. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195- 2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970- 11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
25. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195- 2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970- 11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
26. Reviews on amino acid derived chiral auxiliaries: Studer, A. Synthesis 1996, 793-815. Ager D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997,30,3-10. For individual applications, see also, among others: (a) Denmark, S.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745. (b) Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527-2528. (d) Maligres, P. E.; Upadhyay, V.; Rossen K.; Cianciosi, S. J.; Purick, R. M.; Eng, K. K.; Reamer, E. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 2195- 2198. (e) McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 8. 11970- 11971. (f) Wang, Y.; Hung, A.; Chang, C.; Yan, T. J. Org. Chem. 1996, 61, 2038-2043. (g) Schrader, T. Chem. Eur. J. 1997, 3, 1273-1282. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883-788. (i) Chang, J. W.; Jang, D. P.; Uang, B. J.; Liao, F. L., Wang, S. L. Org. Lett. 1999, 1, 2061-2064. (k) Kim, S. M.; Byun, I. S.; Kim, Y. H., Angew. Chem. Int. Ed. 2000, 39, 728-731.
27. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860. Regarding the influence of allylic 1,3-strain on the structure and reactivity N,N-, N,O-, and O,O-acetals, see: (a) Seebach, D.; Lamatsch, B.; Amstutz, R.; Beck, A. K.; Dobler, M.; Egli, M.; Fitzi, R.; Gautschi, M.; Herradòn, B.; Hidber, P. C.; Irwin, J. J.; Locher, R.; Maestro, M.; Maetzke, T.; Mourino, A.; Pfammater, E.; Plattner, D. A.; Schickli, C.; Schweizer, W. B.; Seiler, P.; Stucky, G.; Petter, W.; Escalante, J.; Juaristi, E.; Quintana, D.; Miravitlles, C.; Molina, E. Helv. Chim. Acta 1992, 75, 913-934. (b) Chu, K. S.; Negrete, G. R.; Konopelski, J. P.; Lakner, F. J.; Woo, N.-T.; Olmstead, M. M. J. Am. Chem. Soc. 1992, 114, 1800- 1812. (c) Axially twisted N-aryl amides: Curran, D. P.; Qi, Hongyan; Geib, S. J.; Demello, N. C. J. Am. Chem. Soc. 1994, 116, 3131-3132. Review: Clayden, J. Synlett. 1998, 810-816.
28. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860. Regarding the influence of allylic 1,3-strain on the structure and reactivity N,N-, N,O-, and O,O-acetals, see: (a) Seebach, D.; Lamatsch, B.; Amstutz, R.; Beck, A. K.; Dobler, M.; Egli, M.; Fitzi, R.; Gautschi, M.; Herradòn, B.; Hidber, P. C.; Irwin, J. J.; Locher, R.; Maestro, M.; Maetzke, T.; Mourino, A.; Pfammater, E.; Plattner, D. A.; Schickli, C.; Schweizer, W. B.; Seiler, P.; Stucky, G.; Petter, W.; Escalante, J.; Juaristi, E.; Quintana, D.; Miravitlles, C.; Molina, E. Helv. Chim. Acta 1992, 75, 913-934. (b) Chu, K. S.; Negrete, G. R.; Konopelski, J. P.; Lakner, F. J.; Woo, N.-T.; Olmstead, M. M. J. Am. Chem. Soc. 1992, 114, 1800- 1812. (c) Axially twisted N-aryl amides: Curran, D. P.; Qi, Hongyan; Geib, S. J.; Demello, N. C. J. Am. Chem. Soc. 1994, 116, 3131-3132. Review: Clayden, J. Synlett. 1998, 810-816.
29. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860. Regarding the influence of allylic 1,3-strain on the structure and reactivity N,N-, N,O-, and O,O-acetals, see: (a) Seebach, D.; Lamatsch, B.; Amstutz, R.; Beck, A. K.; Dobler, M.; Egli, M.; Fitzi, R.; Gautschi, M.; Herradòn, B.; Hidber, P. C.; Irwin, J. J.; Locher, R.; Maestro, M.; Maetzke, T.; Mourino, A.; Pfammater, E.; Plattner, D. A.; Schickli, C.; Schweizer, W. B.; Seiler, P.; Stucky, G.; Petter, W.; Escalante, J.; Juaristi, E.; Quintana, D.; Miravitlles, C.; Molina, E. Helv. Chim. Acta 1992, 75, 913-934. (b) Chu, K. S.; Negrete, G. R.; Konopelski, J. P.; Lakner, F. J.; Woo, N.-T.; Olmstead, M. M. J. Am. Chem. Soc. 1992, 114, 1800-1812. (c) Axially twisted N-aryl amides: Curran, D. P.; Qi, Hongyan; Geib, S. J.; Demello, N. C. J. Am. Chem. Soc. 1994, 116, 3131-3132. Review: Clayden, J. Synlett. 1998, 810-816.
30. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860. Regarding the influence of allylic 1,3-strain on the structure and reactivity N,N-, N,O-, and O,O-acetals, see: (a) Seebach, D.; Lamatsch, B.; Amstutz, R.; Beck, A. K.; Dobler, M.; Egli, M.; Fitzi, R.; Gautschi, M.; Herradòn, B.; Hidber, P. C.; Irwin, J. J.; Locher, R.; Maestro, M.; Maetzke, T.; Mourino, A.; Pfammater, E.; Plattner, D. A.; Schickli, C.; Schweizer, W. B.; Seiler, P.; Stucky, G.; Petter, W.; Escalante, J.; Juaristi, E.; Quintana, D.; Miravitlles, C.; Molina, E. Helv. Chim. Acta 1992, 75, 913-934. (b) Chu, K. S.; Negrete, G. R.; Konopelski, J. P.; Lakner, F. J.; Woo, N.-T.; Olmstead, M. M. J. Am. Chem. Soc. 1992, 114, 1800- 1812. (c) Axially twisted N-aryl amides: Curran, D. P.; Qi, Hongyan; Geib, S. J.; Demello, N. C. J. Am. Chem. Soc. 1994, 116, 3131-3132. Review: Clayden, J. Synlett. 1998, 810-816.
31. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860. Regarding the influence of allylic 1,3-strain on the structure and reactivity N,N-, N,O-, and O,O-acetals, see: (a) Seebach, D.; Lamatsch, B.; Amstutz, R.; Beck, A. K.; Dobler, M.; Egli, M.; Fitzi, R.; Gautschi, M.; Herradòn, B.; Hidber, P. C.; Irwin, J. J.; Locher, R.; Maestro, M.; Maetzke, T.; Mourino, A.; Pfammater, E.; Plattner, D. A.; Schickli, C.; Schweizer, W. B.; Seiler, P.; Stucky, G.; Petter, W.; Escalante, J.; Juaristi, E.; Quintana, D.; Miravitlles, C.; Molina, E. Helv. Chim. Acta 1992, 75, 913-934. (b) Chu, K. S.; Negrete, G. R.; Konopelski, J. P.; Lakner, F. J.; Woo, N.-T.; Olmstead, M. M. J. Am. Chem. Soc. 1992, 114, 1800- 1812. (c) Axially twisted N-aryl amides: Curran, D. P.; Qi, Hongyan; Geib, S. J.; Demello, N. C. J. Am. Chem. Soc. 1994, 116, 3131-3132. Review: Clayden, J. Synlett. 1998, 810-816.
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44. The experiments were carried out with the potassium enolate; however, potassium was beyond the scope of our calcalutions. Therefore, the lithium enolate was taken as a model system.
45. Chelate-induced chirality transfer in the alkylation of potassium amide enolates in the presence of HMPA has also been observed by Evans (e.g., Evans, D. A.; Dow, R. L.; Shih, T. L.; Takacs, J. M.; Zahler, R. J. Am. Chem. Soc. 1990, 112, 5290-5313). Potassium-induced Birch reduction-alkylation sequences were reported by Schultz (e.g., Schultz, A. G.; Wang, A. J. Am. Chem. Soc. 1999, 120, 8259-8260 and earlier lit.)
46. Chelate-induced chirality transfer in the alkylation of potassium amide enolates in the presence of HMPA has also been observed by Evans (e.g., Evans, D. A.; Dow, R. L.; Shih, T. L.; Takacs, J. M.; Zahler, R. J. Am. Chem. Soc. 1990, 112, 5290-5313). Potassium-induced Birch reduction-alkylation sequences were reported by Schultz (e.g., Schultz, A. G.; Wang, A. J. Am. Chem. Soc. 1999, 120, 8259-8260 and earlier lit.)